in: Character, Featured, Manly Lessons

• Last updated: September 26, 2021

The Churchill School of Adulthood: A Prerequisite Class on Becoming the Author of Your Own Life

The Winston Churchill Header.

On Monday, we kicked off the Winston Churchill School of Adulthood with a general discussion of the way in which the master key in growing up well is learning how to combine the seemingly contradictory energies/ideas/interests of both youth and maturity. A swirl of different currents can create a narrative of adulthood that’s interesting, fulfilling, and even a bit electric.

But before we delve into these various currents, let’s begin by exploring the power of being able to create that narrative yourself in the first place. Embracing this power is the prerequisite to everything else. The great gift of life is our ability to make of it whatever we desire – to author our own stories. It is a power and privilege that expands as we mature, become more independent, and have a fuller field of options from which to choose. In growing up lies the potential to construct our own reality – a reality that can be much different than the set of cards we were born with. Every hero’s journey is a tale of the intersection of fate and choice; while we cannot control the former, we can take full advantage of, and heartily relish, the latter.

Beginning here will also let us sketch a brief biography of Mr. Churchill’s life, which will help provide context for the lessons to come. So let us now turn to examining how he exemplified the human potential for being the authors of our own lives.

A Prerequisite Class on Becoming the Author of Your Own Life

An Inauspicious Start

Winston Churchill dapper young boy portrait.

“Churchill had spent his entire life creating an identity from his own audacious imagination, which, as Oscar Wilde observed, was the best way to get through life without suffering through it all. Churchill had made his dream a reality; he had imagined himself into Sir Winston Leonard Spencer Churchill, the greatest statesman of the twentieth century.” –William Manchester, The Last Lion

Imagining himself into a better storyline was necessary for Winston Churchill, as the reality of his early life did not bode well for his future prospects.

He was born in 1874 to parents who were well-off, though not among England’s wealthiest echelon. And though money wasn’t lacking, affection surely was; his parents were distant and remote, and preferred socializing and having affairs to paying much attention to their son. He was left in the care of a nanny, and often passed the time with his favorite game – playing with his toy soldiers on the floor of his bedroom. It was a pastime, Churchill would later realize, that “turned the current of my life.” At the tender age of 7, Winston was uprooted from his childhood nursery and sent to boarding school.

Away at school, his surroundings were hardly more congenial. His biographer, William Manchester, sets the scene: “Sickly, an uncoordinated weakling with the pale fragile hands of a girl, speaking with a lisp and a slight stutter, he had been at the mercy of bullies. They beat him, ridiculed him, and pelted him with cricket balls. Trembling and humiliated, he hid in a nearby woods.”

The classroom brought no respite from stress. Churchill was very bright, but like gifted students in every age, he chafed against the structure of the curriculum. Winston did well in subjects he enjoyed (like English and history), but woefully struggled with those he did not (like Greek and mathematics). This unevenness exasperated Churchill’s teachers, one of which wrote home to his mother to make this dismal report:

“I do not think…that he is in any way willfully troublesome; but his forgetfulness, carelessness, unpunctuality, and irregularity in every way, have really been so serious, that I write to ask you, when he is at home to speak very gravely to him on the subject…Constantly late for school, losing his books, and papers and various other things into which I need not enter—he is so regular in his irregularity that I really don’t know what to do; and sometimes think he cannot help it. But if he is unable to conquer this slovenliness… he will never make a success of a public school…. As far as ability goes he ought to be at the top of his form, whereas he is at the bottom. Yet I do not think he is idle; only his energy is fitful, and when he gets to his work it is generally too late for him to do it well…

[He] is a remarkable boy in many ways, and it would be a thousand pities if such good abilities were made useless by habitual negligence. I ought not to close without telling you that I am very much pleased with some history work he has done for me.”

Churchill bombed his examinations and was shunted into remedial classes. He sat at the very bottom of his grade, a fact he was daily reminded of by the particular way roll was called at the Harrow School he attended as a teen. Each day the students would file through the schoolyard and past their teacher in order of their class rank. Because Churchill’s father was a prominent member of Parliament at the time, visitors to the school would look to see how Winston stacked up against his classmates. Upon glimpsing him, the onlookers would often point and exclaim: “Why, he’s last of all!”

It’s not surprising that Churchill’s school days were the only period of his life that he did not recall fondly:

“Thirty-six terms each of many weeks (interspersed with all-too-short holidays) during the whole of which I had enjoyed few gleams of success, in which I had hardly ever been asked to learn anything which seemed of the slightest use or interest, or allowed to play any game which was amusing. In retrospect these years form not only the least agreeable, but the only barren and unhappy period of my life. I was happy as a child with my toys in my nursery. I have been happier every year since I became a man. But this interlude of school makes a sombre grey patch upon the chart of my journey. It was an unending spell of worries that did not then seem petty, and of toil uncheered by fruition; a time of discomfort, restriction and purposeless monotony.”

Fortunately, Churchill’s opportunities for choosing his own course would start to slowly open before him.

Possibilities for a Life Created Begin to Emerge

Young Winston Churchill in uniform.

To look at any picture of Churchill, young or old, is to realize that despite his reputation for manliness, he was not born naturally masculine or virile. It was an image, a life he had to intentionally choose for himself. He wished to make himself a man, and he succeeded.

After finishing his secondary education, Churchill decided to attend the Royal Military Academy, Sandhurst. He had to take the entrance examinations three times to gain admission, but with much persistence, and the help of a cramming course, he finally made it in. He chose to train for the cavalry (partly because entering the infantry required taking math classes).

At Sandhurst, Winston could finally begin to make his childhood dream of leading men in battle a reality.

As the curriculum was physically demanding, Churchill knew he would need to alter both his physical and emotional constitution to keep up. Since his boyhood, Manchester writes, Winston had “deliberately set out to change his nature, to prove that biology need not be destiny,” and he now doubled his efforts. He willed himself to put aside his frailty and transform himself into an energetic “athlete, projecting the image of a valiant, indomitable bulldog.” Standing at 5’6”, with a chest of 31 inches, the task before him wasn’t easy, and at times he despaired; at age 19, he wrote, “I am cursed with so feeble a body, that I can hardly support the fatigues of the day.” But such pessimistic moments would always quickly pass.

Churchill became an energetic dynamo during field exercises, turned himself into a formidable polo player, and became a man his fellow students loved having on their team for both sports and military exercises. After a childhood of being picked on, he had at last earned the respect of his comrades – the honor of his fellow men. And, having learned the kind of stamina and doggedness he was capable of, he wouldn’t take his foot off the accelerator ‘til the end of his days.

Sandhurst was transformative for Churchill in another way; at last he could study subjects that really interested him! When it came to classes on fortifications, formations, strategy, and martial history, he excelled; Churchill graduated from Sandhurst with honors, ranking 8th out of a class of 150. This “hard, but happy experience” gave Winston a new confidence in himself, as it showed that he “could learn quickly enough the things that mattered.” He passed out of the Royal Military Academy commissioned as a cornet (second lieutenant) in the 4th Queen’s Own Hussars.

Freedom and Opportunity Expand

After Sandhurst, Winston felt the world “opened like Aladdin’s cave.” His life was still subject to the routines and rituals of military discipline, but the possibilities for adventures of his own choosing increased many fold. As did his time for studying whatever he pleased. Though his formal schooling had ended, Churchill began an autodidact phase that would last until his death. As his 23rd birthday approached, “the desire for learning came upon” him, and he began to feel that he was “wanting in even the vaguest knowledge about many large spheres of thought.” Thus while stationed at his first post in India, Winston read books on philosophy, politics, economics, and sociology for 4-5 hours a day. He fell in love with the English language and its power and possibilities. Finally, Winston was utilizing his mind’s great potential to its full extent.

Churchill also relished the opportunity of finally testing in the real world the military skills he had daydreamed about as a boy, and had practiced at Sandhurst. He persistently petitioned his superior officers, and any higher-ups and contacts who would give him the time of day, for a chance to observe and participate in battle, either as a cavalryman or as a war correspondent, and sometimes both. He succeeded in his desire, embedding himself as a journalist with the Spanish in the Cuban War of Independence, fighting on the frontier of India, participating in a cavalry charge along the Nile River, and in the grandest adventure of his youth, being captured in the Boer War, and then escaping to make it back to his men. Churchill was lauded for his courage under fire, as well as the articles and books he wrote about his escapades. His first book was warmly praised, a new experience for a man who had grown up feeling like an academic dunce:

“When the first bundle of reviews reached me together with the volume as published, I was filled with pride and pleasure at the compliments. . .The reader must remember I had never been praised before. The only comments which had ever been made upon my work at school had been ‘Indifferent,’ ‘Untidy,’ ‘Slovenly,’ ‘Bad,’ ‘Very bad,’ etc. Now here was the great world with its leading literary newspapers and vigilant erudite critics, writing whole columns of praise!”

Adulthood was turning out to be a grand journey indeed. And Churchill was just getting started.

Complete Independence: The Hero’s Journey in Full

Though he found his military adventures thrilling, his life was still not positioned exactly as he wished it to be. The wages of a cavalryman were meager, and he found it difficult to avoid going into debt without a regular allowance from his mother. So too, the military still set his schedule for him, so that he was not entirely free to make of each day whatever he willed. Thus, he decided to quit the military to pursue writing more fully and try to win a seat in Parliament:

“I resolved that as soon as the wars which seemed to have begun again in several parts of the world should be ended, and we had won the Polo Cup, I would free myself from all discipline and authority, and set up in perfect independence in England with nobody to give me orders or arouse me by bell or trumpet…

I therefore planned the sequence of the year 1899 as follows: To return to India and win the Polo Tournament: to send in my papers and leave the army: to relieve my mother from paying my allowance: to write my new book and the letters to the Pioneer [a newspaper]: and to look out for a chance of entering Parliament. These plans as will be seen were in the main carried out. In fact from this year until the year 1919, when I inherited unexpectedly a valuable property under the will of my long dead great-grandmother Frances Anne, Marchioness of Londonderry, I was entirely dependent upon my own exertions. During all these twenty years I maintained myself, and later on my family, without ever lacking anything necessary to health or enjoyment. I am proud of this, and I commend my example to my son, indeed to all my children.”

Churchill met his goal of winning a seat in Parliament at age 26. In looking back at this period of his life, he wrote, “Was it wonderful that I should have thought I had arrived? But luckily life is not so easy as all that: otherwise we should get to the end too quickly.”

Churchill’s life indeed had many more twists and turns, ups and downs to come. For twenty years he held several cabinet positions, and was twice considered a potential candidate for Prime Minister, but because of a tide that turned on some of his unpopular stances, he found himself isolated from positions of power during what are known as his “wilderness years.” His chances of ever becoming the PM were considered infinitesimal, and he spent the 1930s focusing on his writing, and making impassioned speeches warning of Germany’s rising power to booing university students and an empty House of Commons.

In due time, of course, the world discovered that Churchill’s disregarded premonitions had been all too true, and at last he found himself thrust into power and leading his countrymen in a legendary battle to save his beloved island home, and the future of democracy as well. A man who had once stuttered and trembled around others gave speeches that enlivened the heart and strengthened the backbone of an embattled nation.

Then, after the war, he was out again, his fellow Englishmen desiring a different man to guide them through the peace, than had shepherded them through the crisis. Churchill was rejected, only to serve as PM once again from 1951-1955. Even after that second tenure, Winston didn’t fade away into an idle retirement, but remained in the House of Commons until he was nearly 90 years old.

And his political career was only one part of how he spent his time over the decades. Whether he was riding high, or on the outs, Churchill was constantly making a rich and varied life for himself. While we remember him as a statesman, he actually made his livelihood almost entirely from his writing. By the end of his life, the boy who had struggled in school had penned 44 books and over a thousand articles.

Oh, and in his spare time, he learned to fly, played polo, gardened, painted, hunted, traveled, stayed faithful to his wife of almost sixty years, and reared four children.

Such was the life of a grown-up glow worm.

Takeaways from Today’s Class

Winston Churchill quote endless moving picture.

It seems to me a truism, that those who have the strongest streak of independence, and who fit least comfortably into the confines of society’s institutions, are those who are least apt to nostalgize their childhood, and most enjoy being an adult. Those who are comfortable with externally-imposed structure, kowtow to authority both in their younger years and as a grown-up, but miss the lack of responsibilities they enjoyed in their youth. But those who chafe at the restrictions and dependency of childhood don’t mind the extra responsibilities that growing up brings…because they’ve chosen these roles themselves. The difference is between those who crave freedom from, rather than freedom to. Churchill belonged to the latter set; the end of his school days, and other people’s rules for him, was the beginning of a world of new possibilities and the best times of his life.

Unfortunately, most adults don’t take advantage of the freedom to create their own lives. When we’re children, we think being an adult will be really cool – we can travel wherever we like! Read whatever we like! Stay up until whenever we want! But then when we grow up, it seems like we’ve simply traded the parental rules and school schedules of our youth for the rules and schedule of our workplace (and the schedule of our kids’ school), and we feel just as hemmed in as we were as kids. Even the self-employed aren’t immune; as a blogger I could hypothetically take off whenever I want, but I’ll be damned if my boss isn’t a tyrannical overlord!

The truth is, that wherever we are in life, we all have pockets of time that we own, and that we could be doing more to actively shape and make the most of. It’s just that so often we default to the path of least resistance. Unbelievably, Americans only use 51% of their paid vacation and paid days off. When we’re not working, and do have free time, rather than pursuing a constructive hobby or side business, we’ll often plop in front of the TV or mindlessly surf the internet. Instead of seeking out good books to read to feed our minds, we default to consuming whatever information happens to pop up in our Facebook feeds. The ironclad rules that governed our childhood are long gone, and yet we still don’t feel fully in control of our lives. We feel swept along by the currents of our responsibilities, so that our lives seem to go by in a unthinking haze – a fog that is ever so often perforated by the question: “Why haven’t things turned out the way I had hoped?”

Takeaway : Authoring an awesome adulthood requires taking the initiative and being intentional. It isn’t just going to happen.

If you want the story of your adulthood to be interesting and engrossing, you’ll need to proactively author it, page by page. While none of us will likely find ourselves at the helm of a nation, we all have areas of our lives where we can be creating more. We create our minds, our thoughts, our habits, our moral code, our routines, our families, our hobbies, and more. In the professional realm, even if you’re not self-employed, you can look for ways to create more autonomy at work. And every step of the way, you can make moves to pivot into positions that will grant you even more freedom and control over your path – more money, more time, more opportunities to do what you really enjoy on the job and away from it. Authoring a better reality, a better story for yourself is something you have to work on constantly; the task is in fact exactly like the way Churchill describes writing a book:

“It was great fun writing a book. One lived with it. It became a companion. It built an impalpable crystal sphere around one of interests and ideas. In a sense one felt like a goldfish in a bowl; but in this case the goldfish made his own bowl. This came along everywhere with me. It never got knocked about in travelling, and there was never a moment when agreeable occupation was lacking. Either the glass had to be polished, or the structure extended or contracted, or the walls required strengthening. I have noticed in my life deep resemblances between many different kinds of things. Writing a book is not unlike building a house or planning a battle or painting a picture. The technique is different, the materials are different, but the principle is the same. The foundations have to be laid, the data assembled, and the premises must bear the weight of their conclusions. Ornaments or refinements may then be added. The whole when finished is only the successful presentation of a theme.”

Churchill’s secret to success was that he continually worked to position himself to reach places where he had the power and opportunity to exercise the full capacity of his energy and imagination. One chapter must lead to the next. It didn’t happen overnight, which is why you have to play the long-game:

Takeaway : Life isn’t a short novella, it’s a long, hefty tome. Never stop working for a satisfying ending.

After studying his life, the British psychiatrist Anthony Storr posited that the source of Churchill’s strength lay in his “inner world of make-believe,” and that in the coming of WWII, his world of imagination “coincided with the facts of external reality in a way that rarely happens to any man.” It’s true that fate helped fulfill Churchill’s long-held dream of leading his countrymen in wartime, but had his life never intersected with those events, his dreams still allowed him to become more, and accomplish more than he would have otherwise.

Churchill never stopped having goals on the horizon to strive for and continually move towards. When he finally achieved his lifelong desire of becoming prime minister, he was 65. As Manchester points out, “five months before he became prime minister he had been eligible to draw an old-age pension. Indeed, he was to be the senior statesman of the war—four years older than Stalin, eight years older than Roosevelt, nine years older than Mussolini, fifteen years older than Hitler.” His associates affectionately referred to him as “The Old Man.” He may have looked mature in years, but beneath the worn exterior there was a little boy who liked to play with toy soldiers on his bedroom floor.

What’s something your 8-year-old self figured you’d be doing by now? Get busy adding it to your story.

Read the Entire Series

The Winston Churchill School of Adulthood Is Now in Session
Lesson #1: Develop a Mighty Moral Code
Lesson #2: Establish a Daily Routine
Lesson #3: Live Romantically
Lesson #4: Cultivate a Nostalgic Love for History
Lesson #5: Don’t Give Up Your Sense of Adventure
Lesson #6: Don’t Be Afraid to Start a Family
Lesson #7: Work Like a Slave; Command Like a King; Create Like a God
Tips on Hustling, Leadership, and Hobbies from Winston Churchill
Conclusion: Thought + Action = An Awesome Adulthood


And now with that introduction and foundation out of the way, next week we will begin to look at the specific energies, perspectives, and methods that helped Churchill author an incredible adulthood for himself. And which can do the same for us.

See you back in class next week!


The Last Lion Trilogy by William Manchester

My Early Life by Winston Churchill

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